


A Few Looks Later

by suckerfordeansfreckles



Series: More than just a First Impression [3]
Category: Supernatural
Genre: ALL THE GOOD THINGS, Developing Relationship, Established Castiel/Dean Winchester, Established Relationship, Falling In Love, First Dates, First Time, Hand Jobs, Kissing, Love, M/M, Public Hand Jobs, Trans Castiel (Supernatural), Trans Male Castiel (Supernatural), Trust, i guess
Language: English
Status: Completed
Published: 2020-11-08
Updated: 2020-11-08
Packaged: 2021-03-08 22:47:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27454471
Author URL: https://archiveofourown.org/users/suckerfordeansfreckles/pseuds/suckerfordeansfreckles
Summary: It’s date eleven, and Cas has picked Dean up and is driving them into the woods, to the small place he found with some friends while hiking years ago. A little clearing just beside the road, where he can drive right into and Dean won’t have to walk.In his trunk, he’s got boxes with food and desert, a picnic blanket and a thermos filled with cold, homemade lemonade.Dean sings along to the songs Cas’ favorite 80s radio station is playing, loud and enthusiastic, his head back against the headrest, and the sun is shining through the windows and lighting him up.Cas feels like his heart might burst.
Relationships: Castiel/Dean Winchester
Series: More than just a First Impression [3]
Series URL: https://archiveofourown.org/series/1671838
Comments: 33
Kudos: 166





	A Few Looks Later

**Author's Note:**

> Hello my friends, I am finally back with a handful of words in an already established universe.
> 
> I hope you like this.

Date three is Mario Kart and Asian food at Cas’ place. Dean beats Cas a lot during the races and is very smug about it, but Cas gets his revenge by laughing over how terrible Dean is at eating with chopsticks.

Date four is mostly sharing funny childhood stories and eating a funky green-blue cake with Charlie and Gilda. Cas is so into the cake, Charlie has to swear to call them when they have shop leftovers again.

Date five was supposed to be a Scrabble night but ends in a lot of kissing on Dean’s couch and a few Scrabble letters poking Cas’ ass when he ends up sitting on the table between Dean’s spread legs, hands in Dean’s hair.

Date six is at the movie theater and Cas is pretty proud about being able to drive again. He’s not particularly as proud about his parking job, but sharp motions and turning the wheel too fast still hurt. Dean cheers him on anyway, assures him that nobody could have done a better job fitting between those cars and smiles at him fondly all the way into the theater.

Date seven is meeting Dean’s brother Sam and Sam’s girlfriend Jess at a small Italian place. Cas is enamored with them, and Dean seems really happy about the way he and Sam connect over university and professors, and Jess and Cas find common ground in their love for painting.

Cas’ brother Gabe bursts in on date eight at Cas’ place and then refuses to leave them alone. They end up watching a few pretty terrible comedies together and stuffing themselves with the caramel popcorn Gabe brought. The night ends up being really nice, even though Gabe’s presence prevents them from the heated make-out they have been anticipating and teasing each other about through texts all week.

Date nine and date ten, well, Cas isn’t so sure they count as dates. Mostly they were filled with talks and kisses that have him dizzy just thinking back. 

He knows about Dean’s past relationships now, knows about his parents and his childhood, knows about how he realized he’s bi, how involved he is in the community. He knows about his favorite things and people and music and movies. And Dean knows all those things about him too. 

But he also knows the shape and feel of every inch of Dean’s mouth and lips now, knows the way Dean whimpers when it all gets too much and they have to take a break. Knows the way Dean feels hard against him. Knows the way Dean makes him feel, makes him ache for touch, when he hasn’t felt this way in ages — or ever, really. Knows how it feels to be scared shitless of going further, but also how comfortable and confident Dean makes him feel. 

It’s date eleven, and Dean has been without a cast for five days now but naturally still struggles with walking.

It’s date eleven, and Cas’ scars are healing nicely and his pain is fading without the pills.

It’s date eleven, and Cas has picked Dean up and is driving them into the woods, to the small place he found with some friends while hiking years ago. A little clearing just beside the road, where he can drive right into and Dean won’t have to walk.

In his trunk, he’s got boxes with food and desert, a picnic blanket and a thermos filled with cold, homemade lemonade. 

Dean sings along to the songs Cas’ favorite 80s radio station is playing, loud and enthusiastic, his head back against the headrest, and the sun is shining through the windows and lighting him up.

Cas feels like his heart might burst.

“Damn, this place is great,” Dean exclaims when they make it through the thicket of trees and arrive by the small clearing. 

Cas shuts off the engine and smiles, happy that Dean seems to be already enjoying this place as much as Cas himself usually does. 

He grabs the blanket from the trunk and helps Dean out of the car even though he huffs about it, and then leads him over into the middle of the field and beneath a big oak tree, where he spreads the blanket.

“Sit,” he tells Dean, who in turn just huffs another laugh but does as he’s told.

“I’m not a dog. Or invalid,” he mumbles, arranging his legs on the blanket.

“I know,” Cas answers simply, turning and grabbing the food from the trunk. “I just want to pamper you a little.”

He spreads the food between them and then settles across from Dean, who’s blushing a delightful pink, and starts to open the tupper boxes one after the other. 

Dean’s face does the cutest things when he watches as Cas pulls out Ellen’s burgers and fries from a box. 

“I thought… as an ode to date one,” Cas says, handing Dean his food.

“God, you’re the best,” Dean mumbles, eyes big. “Date eleven,” he adds quietly, when Cas goes back to unwrapping his own food.

“Hm?”

“Date eleven, today. Told you I’d have you as long as possible. Longer than ten dates, if you have me.” There’s the most gentle of smiles on his lips, and he leans over to press a kiss to Cas’ lips.

“Yeah? Does that mean I’ll get another date after this?” Cas chuckles, leaning in for a second brief kiss.

“We’ll see,” Dean smirks. “Depends on how much you’ll kiss me after this delicious meal.”

“A lot,” Cas promises, and then laughs when Dean sends him a satisfied nod and dives into his burger.

They have apple pie for desert, because Cas knows Dean too well, at this point. The last few pieces are a bit of a struggle, with Dean feeding him bites, watching with dark eyes as Cas wraps his lips around the fork. It’s charged between them. It has been charged for weeks, and both of them have a hard time holding back by now.

When the last bite is gone, Dean puts the cardboard box of pie to the side and reaches over, pulls Cas towards him and into a kiss so soft and cinnamon-sweet, Cas aches with it. 

When he deepens the kiss, Dean moans against his lips, pulls him up and over him until he’s straddling his lap almost like that one memorable time on Dean’s couch. Cas spends a few minutes just enjoying sinking into the kiss and hovering above Dean before he remembers that this time, he doesn’t have to worry too much about hurting Dean, so he allows himself to sit down and kiss him again even harder. 

The second he really sits down, he feels Dean’s budding hardness, and then Dean bucks up against him with a breathless noise.

“Cas,” he breathes, voice rough and needy already, and then he kisses Cas again in a way that makes him forget everything else but the softness of Dean’s mouth and the line of his cock, hard and clearly outlined even through his jeans. “Jesus.”

There’s something swirling in his stomach, moving lower and pulling, and Cas can feel his body starting to react to Dean’s touch, his presence, his words.

“I want,” Cas starts, and then wonders where he was even going. He wants everything with Dean, but he’s not sure what he can ask for already.

When a moan slips from his lips, his first instinct is to be ashamed. But then Dean’s eyes flutter open, and his pupils are blown when he says: “Fuck, you’re so hot.” He kisses Cas again, open-mouthed and wet. 

His hands draw a path down Cas’ sides, over his stomach and down lower. When his fingers find the seam of Cas’ jeans, something inside of Cas shakes apart. His heart is racing, and this time it’s not only fear, it’s want too.

“Can I?” Dean asks carefully, watching Cas’ eyes for clues.

“Yes,” Cas answers, voice a little hoarse with nerves, and then immediately regrets it a little when Dean’s fingers fumble open the button of his jeans and Cas’ heart starts racing again. He’s so glad to know that nobody ever comes by this little clearing, at least.

Dean kisses him even softer than ever before when he pulls down the zipper and pushes Cas’ jeans lower on his hips. “You wanna lie down, Cas?” he asks, and Cas complies, gets off of Dean and lies down on the free space of the blanket. Dean follows as if bound to him, falls down with him until their lips connect again.

“Do you…” Dean starts, voice shaking a little. “How do you feel about taking our shirts off?”

“Sure,” Cas answers, even though something inside him is shaking and sick. He feels good about his chest now, but the scars are still there, still red and prominent, and Dean has never seen them before. 

They’ve talked about Cas’ transition, that he’s been on T for a few years by now and that top surgery was his first surgery ever. About how… how he feels, with everything being the way it is. Dean knows more than anyone ever has, and Cas knows he will be gentle with him. Knows he won’t laugh about scars or wrinkle his nose or be weird about it. Or hopes so, at least.

He thinks he knows Dean by now. But there’s still that tiny bit of worry shaking under his skin. That feeling of not looking quite like who he feels he is. Of not being quite what Dean wants him to be, expects him to be. It rears its head sometimes, but usually Dean is very good at kissing it quiet and making the feelings in Cas’ chest turn from spiky ice to blooming warmth in an instant.

Dean’s hands are at the seams of his shirt and pushing it up to expose his stomach when Cas comes back from his thoughts into reality. Dean’s already out of his own shirt and Cas gets lost for a while in the creamy skin of Dean’s broad chest and the softness of his tummy. “You’re beautiful,” he murmurs, and then he gets to watch the prettiest blush spread all the way down to Dean’s pecs. 

“Says you,” Dean grins, trying for cocky but ending up soft. And then his hands are back and pulling on Cas’ shirt, loving but insistent. “I want to see you, please.”

Cas helps and sits up, waits until Dean has his shirt pulled off of him entirely before sinking back down. Dean’s eyes are soft and wide when he casts them over Cas’ face, down his neck and over his chest, his stomach. Before Cas can even decide how he feels about it, Dean’s ducking down and peppering whispers of kisses all along the path his eyes drew earlier. When he reaches Cas’ chest he’s especially gentle, and Cas’ heart sings. 

“I want you so much,” he mumbles into the skin of Cas’ tummy, and it’s all Cas can do to pull him up and into another mind-numbing kiss. 

The heat pooling in Cas’ stomach isn’t stopping, and he suddenly desperately needs to touch Dean. His fingers are already working open the button of Dean’s jeans when his lips manage to pull away and form some words: “Can I? Need to touch you.”

Dean nods eagerly, helping as Cas pulls off his pants and then removing Cas’ pants all the way. They are left in nothing but their boxers, Dean’s a deep red against Cas’ light blue ones, and Cas is momentarily distracted by it until Dean leans back up over him and kisses him once more.

There are fingers dancing along the seam of his underwear and Cas briefly thinks that maybe he has never wanted anything as much as he wants Dean’s hands on his bare skin right now. He decides to take the first step, pushes his hands down to cup Dean’s dick through his underwear, and when he gives it a little squeeze, neither of them can contain their moans. 

Broken away from each other’s lips, Cas grows bold enough to fumble his way into Dean’s underwear and in turn gets to watch the way Dean’s head drops down against Cas’ chest with a soft groan when he first touches him without any barriers between them. 

“Fuck, Cas,” he sighs, twitching in Cas’ grasp. “I’ve been thinking about this so much.”

Some wiggly-happy form of pride surges through Cas’ chest, and he starts to carefully stroke Dean’s cock and listen to the noises he makes. He doesn’t get far in testing what movements Dean enjoys, because seconds later Dean wiggles his hand into Cas’ pants and the second Cas feels his fingers, everything else fizzles away.

Dean starts with careful brushes down lower and lower, until he arrives where Cas is hot and pulsing and a little wet for him. His mouth finds Cas’ lips again, kisses him dizzy, while his fingers work between Cas’ legs and find his most sensitive parts.

“Is this okay?” Dean speaks against his lips, breath hot. 

“Yes,” is all Cas can get out. “Please, yes.”

And then Dean starts circling his fingers around Cas’ cock and stroking him in a way that has him seeing stars in mere minutes. 

“You’re so hot,” Dean murmurs, only breaking their kisses when he mumbles praise of pants for breath. “I can’t wait to suck your dick someday.”

At that, a shiver runs through Cas’ body, breath, heart and hands trembling, and only then does he realize that he’s still just holding onto Dean’s cock. He tries to focus on making this good for Dean, through the haze of pleasure that’s washing over him with every stroke of Dean’s hand. He moves his hand, lets his fingers dance over the length of Dean’s dick, lets his thumb brush through the wetness on the head. 

Dean trembles against him at a particular twist of his wrist, so Cas repeats it again and again, enjoys the way Dean shivers and shakes and gets unintelligible and pants against his mouth. 

“Just like that, yes, yes, yes,” Dean breathes after a few minutes, his cock pulsing in Cas’ hands until suddenly all his moans and panting accumulate in a low, wonderful groan and he stills, his dick jumping as he spills across Cas’ side and onto his stomach.

His eyes are pressed shut during it, but then they flutter open again and reveal something wild. “Fuck, Cas, sorry. Didn’t even consider,” he slurs, nodding down towards Cas’ stomach.

All Cas can do is grin and lean up to kiss him again, breathless and a little proud with the way he just made Dean come undone in minutes. “Please,” he whispers against Dean’s lips. “Touch me again?”

And he doesn’t have to wait, since Dean’s fingers are still resting against him and start to move immediately with his plea. It’s kind of a miracle, the way Dean makes him feel and ache and want. It doesn’t take much, with the way Dean’s come is still warm on Cas’ side and the sparks Dean’s fingers are sending down his spine. A few more strokes, and Cas comes, pulsing and spasming and kissing Dean hard and biting. 

In the aftermath, Cas slack and gasping for breath on his space on the blanket, Dean sinks down on top of him, head on Cas’ heart. 

“Wow,” he says, turning a little to press a kiss to Cas’ shoulder. “Holy shit.”

“Yeah,” Cas agrees, moving his hand until his fingers are buried in Dean’s hair. “That was — amazing.”

“Mhm,” Dean answers, voice a little cocky. “So you’d try that again, with me?”

That contradiction in tone and words startles a laugh out of Cas, and subsequently jostles Dean a little on top of him. “A hundred times,” he answers, massaging Dean’s scalp. “A thousand.” 

“Awesome,” Dean sighs, burying his face against Cas’ skin. 

It takes a while before the cooling come on their stomachs bothers them enough to make them move apart and clean up.When they head home in Cas’ car, for the first time so far, they both head to Dean’s place. For the first time, they get to fall asleep for the night next to each other, arms and legs tangled and hearts warm and bright.

**Author's Note:**

> If you enjoyed this, I'd be very, very happy and lucky if you left a comment here or on my [Tumblr](https://suckerfordeansfreckles.tumblr.com/post/634235829910372352/a-few-looks-later-read-on-ao3-relationship). I did take the picture I used for the banner by myself !! And find it quite pretty! If you wanna check it out on Tumblr!
> 
> I'm sending all of you love and health!!


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